Well to answer this for Key West, I guess it depends on what you're after.

PT's Latenight on Caroline...Near corner of Caroline and Grinnell St. is a sports bar with a WIDE variety of food that has good prices. It's right around the corner from the city parking garage and PT's can validate your parking for 1 hour of dining. I've lived here in Key West for 8 years and never had a bad meal there.

Alonzo's-(on front street by the seaport district) has parking next door and unadvertized 1/2 all appetizers from 5-6PM caters towards seafood but has other choices but expensive if you don't catch the 5-6pm or lunch time.

Blue Heaven-(corner of Thomas and Petronia) has great food/drinks is outdoor dining and as someone else has stated there is dirt/sand/woodchips on the ground where you dress up a little but don't wear good shoes unless you don't mind dusting them off after the meal. Also if cats/chickens scurrying around under your feet from time to time and around the area turns you off then it's not gonna be your cup of tea but awesome Sunday brunches, breakfast anytime and great dinner meals.

El Sibonney-(corner of whitehead and Catherine st) a little off the beaten path and is in a residential area but has Authentic cuban food with great prices. Ditto on the great meals every time I've ate there.

1/2 shell raw bar (very close to PT's) mainly seafood dining with nightly specials (Weds.-all you can eat snow crab) decent prices and right on the water.

Michael's Resteraunt-(corner of Southard and believe Margaret) Variety of foods kind of pricey but very good steaks and duck dishes.

Mangia Mangia-large white bldg on left side of road across the road from Michael's. If you don't like Garlic or italian food stay away!! They have fresh made pasta every day and love to use garlic on the food. You can choose several kinds of pasta and different sauces depending on your preference...not like alfredo or thick sauce italian style dinners.

Basically when you get into town tune to channel 18 on your tv in the room and it will show you many of the places I've talked about and different things to do while you're here. Any other questions specific to Key West you may have I'll try my best to fill you in and one word of warning since someone mentioned Key West T-shirts...they're everywhere and be sure to get the price upfront if you're doing something custom and ONLY PAY CASH!! I've read several times in paper where visitors have come and bought 3 for $10 t-shirts and got $100 or more charge on the card when they got home and has been the target of undercover police stings...most places are pretty reputable down here as the whole town thrives on tourism but especially at the t-shirt shops try to use cash when possible.